5,5&#39;-dihydroxydiamyl ether



Patented Apr. 19, 1949 UNITED STATES PATENT OFFICE 5,5'-DIHYDROXYDIAMYL ETHER No Drawing. Application May 18, 1948, Serial No. 27,816

1 Claim.

(Granted under the act of March 3, 1883, as amended April 30, 1928; 370 O. G. 757) This application is made under the act of March 3, 1883, as amended by the act of April 30, 1928, and the invention herein described, if patented in any country, may be manufactured and used by or for the Government of the United States of America for governmental purposes throughout the world without the payment to us of any royalty thereon.

This invention relates to 5,5'-dihydroxydiamyl ether having the formula Preparation of 5,5'-dihydro:z:ydiamyl ether In a large flask provided with a reflux condenser was placed a solution containing 41.2 g. (0.15 mole) of diethyl oxydivalerate in 480 cc. of absolute ethanol. To this was added 42 grams (1.83 moles) of sodium in large pieces. Cooling in an ice bath was necessary during the first stages of the reaction. When the initial vigor of the reaction had subsided, the mixture was heated on a steam bath for several hours until all the sodium dissolved. Water (180 cc.) was then added to the cooled mixture and the alcohol distilled off. More water (250 cc.) was added and the oil layer which separated was removed. Distillation at reduced pressure gave 5,5-dihydroxydiamyl ether having the formula as a colorless, viscous liquid, B. P. 141-142 C. (0.5 mm.) M. P. 16l8 C. It is soluble in water and ether, insoluble in benzene. The yield Was 21 grams.

Other 'diesters of oxydivaleric acid, such as dibutyl oxydivalerate, ditetrahydrofurfuryl oxydiv-alera'te, and the like may be reduced in a manner similar to that described in the above example to form the desired product.

The procedure of the above example maybe varied as to proportions of reactants and. reaction conditions, these variations being apparent to those skilled in the art.

Although in the above example the reduction of the esters by means of sodium and alcohol is described, other means of hydrogenation, for example, catalytic hydrogenation, may be employed.

Having thus described our invention, we claim:

5,5-dihydroxydiamyl ether having the formula.

The following references are of record in the file of this patent:

UNITED STATES PATENTS Name Date Briveault et al. Oct. 15, 1907 OTHER REFERENCES Muller et al., Mon-atshef-te fur Chemie. vol. (1928) pages 106-108.

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